Fall of Philadelphia
1378 CE.
Shown on the map at 38.350°, 28.517°.
The Fall of Philadelphia in 1390 marked the conquest of the last independent Byzantine city in Asia Minor by the Ottoman Empire. The city was subjected to a siege by the Ottoman forces, which included a Byzantine contingent led by Manuel II Palaiologos and John VII, who were political hostages of Sultan Bayezid I.
Text from the Wikipedia article Fall of Philadelphia, licensed CC BY-SA 4.0.